City Councilor John Connolly’s bold move

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It says everything about Tom Menino’s five terms in office that the boldest act one can commit in Boston politics may be to run against him.

Consider that a generation of elected officials have gone out of their way to declare that under no circumstances would they ever consider running against the city’s five-term patriarch. Though the supplicants generally cite respect and affection as their driving forces, surely another consideration is the fear of being crushed like a bug.

Interesting, then, that Councilor John Connolly has become the first serious politician to declare that he is considering running for mayor this year. By his own admission, he is already in the process of planning a campaign.

Equally bold is that he is running on a platform of reforming the Boston schools, never mind that education remains easily the city’s most divisive political issue, fraught with overtones of race and class.

Menino, of course, is still slowly returning to full speed after two months of hospitalization late last year. He has not lifted a finger to begin a campaign, prompting quiet speculation that maybe — just maybe — he isn’t fully decided on running again.

“His decision really doesn’t matter to me,” Connolly said. “I respect him deeply, but for me this is about our schools and our families.”

Connolly, 39, has made education a centerpiece of his work on the council since he was first elected in 2007. He has spent the past couple of years politely pummeling Superintendent Carol R. Johnson and the leadership of the Boston Public Schools. While Connolly has been criticized in some corners for attempting to score easy political points, the fact is that he has often said what others have simply been afraid to say.

“What I see is a top-heavy bureaucracy on Court Street that spends $1 billion a year and misses the mark,” Connolly said last week. “I would really change the way schools operate. I would place a real emphasis on principal recruitment and quality.”

In fact, the schools have improved under Menino, though not at a pace that satisfies anyone, including him. Right now, the department is wrestling with its most sensitive issue, school assignment. That issue has historically pitted neighborhood against neighborhood and class against class. The School Committee is considering plans that would reduce busing and place more children in neighborhood schools.

Connolly, who has been an outspoken advocate of neighborhood schools, says the proposals under consideration don’t go far enough. But he added that he understands the tension that surrounds the issue.

“On the one hand, there’s no faith that the school department will deliver quality schools in every neighborhood,” he said. “On the other hand we have huge middle-class divestment. I did 50 sit-downs with groups of parents, and the concerns parents have in Roxbury are the same as the concerns in West Roxbury.”

Connolly estimates that he will need $1 million to run against Menino — far more than any Menino opponent has ever been able to raise. (He starts with roughly $300,000 in the bank.) He knows he must put together a coalition of young voters and voters who often sit out city elections.

“I’m going to have to run an unconventional campaign,” he said. “And I’m going to have to raise money in stages, because I have to convince people that I can win.”

That is, he has to convince people that he can do what Peggy Davis-Mullen and Maura Hennigan and Michael Flaherty could not: seriously challenge one of the the most popular mayors in the city’s history.

Connolly claims to relish the challenge. “I really do like the guy and I really respect him,” he said of Menino. “But I think there’s an energy missing in city government.”